| Identification | Back Directory | [Name]
E-64C | [CAS]
76684-89-4 | [Synonyms]
E-64C
NSC 694279
E-64c, EP 475
Loxistatin acid
anecarboxylicacid
ep475(enzymeinhibitor)
Loxistatin Acid (E-64C)
Inhibitorforthiolprotease
NSC 694279 Loxistatin Acid
E-64-c Loxistatin acid NSC 694279
(2s-(2-alpha,3-beta(r*)))-mino)carbonyl)
L-TRANS-EPOXYSUCCINYL-LEU-3-METHYLBUTYLAMIDE
NSC 694279 LOXISTATIN ACID; EP 475;E64C;E 64C
(2S,3S)-TRANS-EPOXYSUCCINYL-L-*LEUCYLAMI DO-3-METHYL
(2S,3S)-TRANS-EPOXYSUCCINYL-L-LEUCYLAMIDO-3-METHYLBUTANE
(2S,3S)-L-TRANS-EPOXYSUCCINYL-L-LEUCYLAMIDO-3-METHYLBUTANE
(L-3-TRANS-CARBOXYOXIRANE-2-CARBONYL)-L-LEUCINE (3-METHYLBUTYL)AMIDE
(+)-(2s,3s)-3-((s)-3-methyl-1-(3-methylbutylcarbamoyl)butylcarbamoyl)-2-oxir
oxiranecarboxylicacid,3-(((3-methyl-1-(((3-methylbutyl)amino)carbonyl)butyl)a
(1S,2S)-2-(((S)-1-(Isopentylamino)-4-methyl-1-oxopentan-2-yl)carbamoyl)cyclopropanecarboxylic
(2S,3S)-3-[[(1S)-1-(3-Methylbutylcarbamoyl)-3-methylbutyl]carbamoyl]oxirane-2-carboxylic acid
(2S,3S)-3-(((S)-1-(isopentylaMino)-4-Methyl-1-oxopentan-2-yl)carbaMoyl)oxirane-2-carboxylic acid
(2S)-3β-[[[(S)-3-Methyl-1-[[(3-methylbutyl)amino]carbonyl]butyl]amino]carbonyl]-2α-oxiranecarboxylic acid
2-Oxiranecarboxylicacid,3-[[[(1S)-3-methyl-1-[[(3-methylbutyl)amino]carbonyl]butyl]amino]carbonyl]-,(2S,3S)- | [Molecular Formula]
C15H26N2O5 | [MDL Number]
MFCD00132882 | [MOL File]
76684-89-4.mol | [Molecular Weight]
314.38 |
| Chemical Properties | Back Directory | [storage temp. ]
−20°C
| [solubility ]
≥31.4 mg/mL in DMSO; insoluble in H2O; ≥111.8 mg/mL in EtOH | [form ]
White to off-white solid | [color ]
White to off-white | [biological source]
synthetic (organic) | [InChI]
InChI=1S/C15H26N2O5/c1-8(2)5-6-16-13(18)10(7-9(3)4)17-14(19)11-12(22-11)15(20)21/h8-12H,5-7H2,1-4H3,(H,16,18)(H,17,19)(H,20,21)/t10-,11-,12-/m0/s1 | [InChIKey]
SCMSYZJDIQPSDI-SRVKXCTJSA-N | [SMILES]
O1[C@H](C(N[C@H](C(NCCC(C)C)=O)CC(C)C)=O)[C@H]1C(O)=O |
| Hazard Information | Back Directory | [Description]
E-64c is an active metabolite of the protease inhibitor E-64d (Item No. 13533).1,2,3,4 E-64c inhibits the cysteine proteases cathepsin B, cathepsin H, and papain but not the serine proteases trypsin, chymotrypsin, or elastase.5,6 It reduces the autocatalytic activity of the foot-and-mouth-disease virus (FMDV) leader protease when used at concentrations ranging from 0.1 to 1 mg/ml.3 E-64c reduces infection of HEK293T cells by an HIV-based virus system pseudotyped with severe acute respiratory syndrome coronavirus (SARS-CoV) surface glycoprotein, also known as the spike glycoprotein, in a concentration-dependent manner.4 | [Uses]
Cell-impermeable epoxysuccinyl peptide inhibitor of calpain and other cysteine proteases. Inhibits calpain and cathepsins B, H, and L. | [Definition]
ChEBI: E-64c is a leucine derivative. | [in vivo]
The t-1/2 of plasma E-64c is 0.48 hours. The hemodynamic effects of E-64c are absent at this dose. Using two way analysis of variance, the effects of reperfusion (p=0.0016) or E-64c (p=0.0226) per se on infarct size are significant. In comparing Group A with Group B and Group C with Group D, the depletion of CPK in the E-64c treated groups (Groups A and C) is slightly less than in the vehicle-injected groups (Groups B and D). The insufficient effect of E-64c alone may be explained by the early administration and relatively short t-1/2. Since the effectiveness of NCO-700 has been established,6),7) our findings might indicate a small but beneficial effect of E-64c on infarct size and CPK content[2]. | [target]
cathepsins B | [IC 50]
Cathepsin C | [References]
[1] Y SHOJI-KASAI. Thiol protease-specific inhibitor E-64 arrests human epidermoid carcinoma A431 cells at mitotic metaphase.[J]. Proceedings of the National Academy of Sciences of the United States of America, 1988, 85 1: 146-150. DOI: 10.1073/pnas.85.1.146
[2] WILLIAM R ROUSH . Design, Synthesis and Evaluation of d-Homophenylalanyl Epoxysuccinate Inhibitors of the Trypanosomal Cysteine Protease Cruzain[J]. Tetrahedron, 2000, 56 50: Pages 9747-9762. DOI: 10.1016/s0040-4020(00)00882-6
[3] L G KLEINA M J G. Antiviral effects of a thiol protease inhibitor on foot-and-mouth disease virus.[J]. Journal of Virology, 1992, 66 12: 7168-7175. DOI: 10.1128/jvi.66.12.7168-7175.1992
[4] GRAHAM SIMMONS. Inhibitors of cathepsin L prevent severe acute respiratory syndrome coronavirus entry.[J]. Proceedings of the National Academy of Sciences of the United States of America, 2005: 11876-11881. DOI: 10.1073/pnas.0505577102
[5] A J BARRETT. L-trans-Epoxysuccinyl-leucylamido(4-guanidino)butane (E-64) and its analogues as inhibitors of cysteine proteinases including cathepsins B, H and L.[J]. Biochemical Journal, 1982, 201 1: 189-198. DOI: 10.1042/bj2010189
[6] M TAMAI. In vitro and in vivo inhibition of cysteine proteinases by EST, a new analog of E-64.[J]. Journal of pharmacobio-dynamics, 1986, 9 8: 672-677. DOI: 10.1248/bpb1978.9.672 |
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Spectrum Chemical Manufacturing Corp.
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